Efficient synthesis and biological activity of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

Autor:	Kohei Ohata, Shiro Terashima
Rok vydání:	2009
Předmět:	Stereochemistry Organic Chemistry Substituent Enantioselective synthesis Absolute configuration Total synthesis Biological activity Biochemistry Chemical synthesis chemistry.chemical_compound chemistry Drug Discovery Enantiomer Antibacterial agent
Zdroj:	Tetrahedron. 65:2244-2253
ISSN:	0040-4020
DOI:	10.1016/j.tet.2009.01.054
Popis:	The title total synthesis was achieved by employing deconjugative asymmetric α-sulfenylation of the chiral 3-(α,β,γ,δ-unsaturated acyl)oxazolidin-2-one with a 3,3-dimethoxypropyl methanethiosulfonate as a key step. From the biological activity assay carried out using the title compounds, it appeared evident that in vitro antibacterial and mammalian type I FAS inhibitory activity can be cleanly separated by changing not only the substituent at the C 3 -position but also the absolute configuration at the C 5 -position, and that unnatural ( S )-(−)-3-demethylthiolactomycin and its congeners might be usable as selective mammalian type I FAS inhibitors.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2f176e16aa08e7a6c18a94a0ccbdcb51 https://doi.org/10.1016/j.tet.2009.01.054 Zobrazit plný text záznamu Full Text from ScienceDirect